Offshoring in Uruguay, South America’s Little Secret

James —  April 13, 2017 — Leave a comment

Expensifiers at Pecana cafe in Montevideo, one of our favorite 10 AM spots

If you’re unfamiliar with our annual Expensify Offshore expeditions, we have a dedicated webpage here to help spark the flame! Otherwise, some tl;dr background:

  1. A complete Expensify Offshore spans four weeks, and occurs once per year. It is always opt-in, meaning any employee can elect not to attend, partially attend, or fully attend.
  2. The employees vote democratically on the destination, which at bare minimum must be internet-friendly and relatively easy on the wallet.
  3. The company coordinates and communicates the essentials, including general itineraries, to-and-from travel, basic lodging, and special events.
  4. Employees self-select to lead or support priority projects dictated by a mix of customer needs and personal interest. The projects are optional, supplementary to daily responsibilities, and ideally completed during the time abroad.


The Arrival

I was a couple days early to Expensify Offshore 2017 in Uruguay.

After six feature films in the nosebleeds of Copa Airlines and a taxi ride at the mercy of Google Translate, I stumbled out onto Montevideo’s Calle Blandengues around 2 AM local time. Historically, this was a Jewish neighborhood and absolutely worth a morning wander, so I left my curiosities for the moment in favor of meeting my Airbnb host, Ramiro.

Ramiro had some serious neck tattoos. The kind of neck tattoos that make you want to be friends with someone just because, well, it’s probably better that way. Upon introduction, I instinctively defaulted to my bread and butter in any foreign country – the smile and thumbs up. Ramiro led me around his apartment like an apprentice, pointing out the obvious – shower, kitchen sink, toilet, light switches, and finally my bedroom. Smile. Thumbs up. I tossed my backpack on the bed and examined it distantly, expecting a suitcase nearby while mentally checking off my list of belongings. But I had been told over and over that one bag was “all you need for the month…seriously.” And so it was.

The next morning, I took to the cobblestones of Ciudad Vieja (Old City) for the weekend. I sampled vacio (flank steak) at the Mercado del Puerto, witnessed an impromptu candombe (traditional Uruguayan drum and dance) session, thoroughly failed to switch my phone to a local SIM card, and of course, toured my home turf. What a perfectly tame preview of the month to come.


Teatro Solís (Solís Theatre), the artistic gem of Uruguay in Montevideo’s Old City

My coworkers would trickle in on flights throughout the days and weeks that followed, a delicate dance between business and travel directed by Expensify’s people ops and management teams. The logistical architecture of Offshore had hardened into habit over the years, but our current team – upward of 100 employees worldwide – was at its historical peak. And, as tradition decreed, we would switch locales regularly to experience Uruguay’s healthy mix of foreign flavors. Easy enough.


Patrolling the streets for paper receipts

On the Move

From Montevideo, we ping-ponged east along the Uruguayan coast, frequenting a veritable carousel of hostel bunks, sandal showers, and same-day lavaderos (laundries) on the cheap.


Success Coaches weekly sync at the “office” in Punta Ballena

The WhatsApp channels roared to life with chatter:

Anyone at a cafe close by with outlets and AC?

Can someone grab my laptop charger from the hostel?

Anybody know when the laundromat opens?

Where’s the best place for a chivito?

Who wants to go kiteboarding this weekend?

How do you say “expense reports that don’t suck” in Spanish?

Alongside the novelty of navigating a new location each week, we maintained critical routines that created a sense of normalcy. Among them, each morning we sprinted through the status of 20+ offshore projects at our 10AM standups.


Makeshift workstations at Jacinto cafe in Montevideo

Somewhere between weeks three and four, just as the heads-down hammering on keyboards grew to a crescendo, a premium sampling of heavy hitters began rolling out:

  • Mobile Approval: The golden child of Joe and Bruno on our Mobile team, this feature was fully rolled out in mid-March to all iOS and Android users. On-the-go productivity has leveled up – and it only takes a few taps through your Expensify Inbox!
  • New Partner Functionality: Spearheaded by one of our most seasoned engineers, Florent, this concept project is already live in the product and guaranteed to delight partners of all types. For starters, partners can now foot the bill for their clients and rebill that expense easily. We also smoothed out client setup, created enhanced reporting, and upgraded tracking capabilities.
  • SmartScan 2.0: A massive endeavor by yet another veteran powerhouse engineer, the bulk of this upgrade will take place “under the hood”…but don’t think you won’t hear the engine rumble when it’s done. Expect your SmartScanned receipts to benefit from increased processing speed and accuracy worldwide as we tighten the bolts on our shiny upgrade!
  • ExpensiCon II: If you remember ExpensiCon I in Maui, you’re probably anxious to hear about what’s in store for the second go-round. Well, fear not. Bob and Lindsey put in some serious hours to prep for the announcement of ExpensiCon II: Bora Bora! Be sure to check out the video here for a little preview of paradise.
  • Receipt Integration Expansion: Building off the initial success of seamless receipt integrations with Uber and HotelTonight, we’re claiming fresh territory under the guidance of our newest business development hire, Matt. From parking to that pre-flight beef jerky, paper receipts will feel the burn as Expensify intelligently imports their digital counterparts in near real-time.

A Brief Look Back


The Punta del Este cityscape

Closing out my fifth month as an Expensify employee during Offshore 2017, I had just enough background on our team to keep my astonishment at bay. We got some major shit done. It was the type of progress that could only be made face-to-face, in one timezone, around the clock. It was the type of progress that would otherwise take months of back-and-forth between international offices over email, Slack, video, and the like.

Don’t get me wrong. Offshore is a perk, and we enjoy the hell out of our time abroad. But unlike most perks, it’s built on years of DIY tradition. From four individuals navigating the underground cisterns of Istanbul in 2008 to 100+ teammates taking over the cafes of Montevideo in 2017, the company and its people have crafted a legacy of learning by doing. To me, this is exactly where the value lies – the company simply hands you a few tools, gives you a push, and says, “Now go figure it out.” It’s sometimes ugly, many times scrappy, and most times worth a laugh…but it’s always a lesson learned and progress made. It brings back the thrill and velocity and hyperfocus of startup life that can occasionally escape us at home in the midst of comfort and routine.

The entire Offshore operation from end-to-end reveals in one whirlwind month what Expensify can accomplish in its most pure and raw form. It’s a yearly reminder to ourselves – as individuals and as a team – that we can always do more.


Sunset at Casapueblo, applauded nightly

Want to join us on our next adventure? We’re hiring in San Francisco, Portland, London, and Melbourne for roles across the board



I ended up in SF by way of Chicago and Michigan. You can find me checking out new restaurants, watching Netflix, playing soccer, running, or laughing. Sometimes I can do it all at once!

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